The trick is to be patient and look in lots of places -- and let people know you're looking. Years ago I somehow found a guy on the east coast of the US who sold older used test equipment. I'm near the west coast of the US, so I wasn't able to see his stuff. But he guaranteed satisfaction and fixed things up before sending them out. His name was Chase Hearn; I don't know if he's still alive, but I sure was happy with the instruments I bought from him. He knew how to fix the older equipment and, I could tell, loved to collect it himself. There have to be others like him -- the trick is finding them.

Spend time studying prices on ebay and elsewhere. Over time, you'll get a good idea of what things are worth. Forget about the prices the used equipment companies charge -- they want much more than the typical hobbyist can afford (they're aiming at businesses who have more cash). You'll see what things sell for on ebay and that will help you decide what you're willing to pay for something. I found an HP E3615A power supply in new condition for $100 on ebay and I was the only bidder. This was a steal as far as I was concerned. I use it more than any of my other instruments.

As to the scope, you can be happy with either digital or analog. I would suggest trying before you buy if you can, as you can learn a lot about a scope in 5 or 10 minutes of playing with it. One thing to think about is how you're going to use the scope. For example, I virtually always want either a picture or a digital image of the scope's screen for documentation purposes. That means I either have to take a picture of the screen with my digital camera on my older scopes or stick in a flash drive and capture the screen using the front panel of the scope. This information is often used in reports to other people, so that's one of my important requirements. If I was just using the scope for instantaneous decision making and troubleshooting, pictorial output might not be as important.

The older analog scopes, especially made by the bigger names, probably have better documentation. For example, my 1970's Phillips scope, which I bought new, has a beautiful manual complete with detailed schematics and troubleshooting information. Most of the scopes today are made in China and, at least for the ones I've seen, the documentation is poor and sometimes not even understandable. And you'll likely never see a schematic. If you buy something at very low cost and it fails, it's likely that you'll be out of luck at trying to get it fixed -- it will probably be most cost effective just to buy another scope.

I use a guy in South Georgia called Test Parts. He sells cleaned up school and indistrial closings type equipment. He is very reasonable and passes on a good deal just about every time. I think his deal is get the stuff, clean it up and fix as needed total it up and add 10.00. I got a Beckman 9020 Scope and 9010 Function Gen together for 80.00 delivered. Couldnt pass it up. The 9020 is a 20MHZ 2 channel scope with self calibration and basic component testing on board. The 9010 has square, saw and sine waves at any freq over 8 ranges. Now the trick is to become proficient at using em properly!!! A task in itself since I am just learning electronics and micro controller programming too. Yes I am a glutton for punishment...
Bob

The subject comes up now and again, and I'll recommend Ham Cons held in your area. Hams as a group are a gabby bunch, and you will get a complete history, probable future, comparison with his neighbor (who will also chip in his 2¢). Basically you'll know what you're buying.

Thanks for the recommendation, I checked out Test Parts and it seemed they focus on test accessories. The section on test equipment, didn't really have any test equipment, probably have to hit the site at the right time. Thanks